diff --git a/src/filesystem/__tests__/path-utils.test.ts b/src/filesystem/__tests__/path-utils.test.ts
index 5530cba1c3..3f6072377b 100644
--- a/src/filesystem/__tests__/path-utils.test.ts
+++ b/src/filesystem/__tests__/path-utils.test.ts
@@ -354,6 +354,17 @@ describe('Path Utilities', () => {
       expect(result).not.toContain('\\');
     });
 
+    it('normalizes bare Windows drive letters to the drive root on Windows', () => {
+      Object.defineProperty(process, 'platform', {
+        value: 'win32',
+        writable: true,
+        configurable: true
+      });
+
+      expect(normalizePath('C:')).toBe('C:\\');
+      expect(normalizePath('d:')).toBe('D:\\');
+    });
+
     it('should handle relative path slash conversion based on platform', () => {
       // This test verifies platform-specific behavior naturally without mocking
       // On Windows: forward slashes converted to backslashes
diff --git a/src/filesystem/path-utils.ts b/src/filesystem/path-utils.ts
index 50910b995b..6ab5a5969b 100644
--- a/src/filesystem/path-utils.ts
+++ b/src/filesystem/path-utils.ts
@@ -77,6 +77,12 @@ export function normalizePath(p: string): string {
     p = p.replace(/\\\\/g, '\\');
   }
 
+  // On Windows, if we have a bare drive letter (e.g. "C:"), append a separator
+  // so path.normalize doesn't return "C:." which can break path validation.
+  if (process.platform === 'win32' && /^[a-zA-Z]:$/.test(p)) {
+    p = p + path.sep;
+  }
+
   // Use Node's path normalization, which handles . and .. segments
   let normalized = path.normalize(p);
 
@@ -116,3 +122,4 @@ export function expandHome(filepath: string): string {
   }
   return filepath;
 }
+